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Probing the Efficiency of N-Heterocyclic Carbene Promoted O- to C-Carboxyl Transfer of Oxazolyl Carbonates.
- Source :
-
Journal of Organic Chemistry . 4/4/2008, Vol. 73 Issue 7, p2784-2791. 8p. 2 Diagrams, 8 Charts. - Publication Year :
- 2008
-
Abstract
- Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 mm at <1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency. [ABSTRACT FROM AUTHOR]
- Subjects :
- *CARBENES
*HETEROCYCLIC compounds
*CARBONATES
*SALTS
*CATALYSIS
Subjects
Details
- Language :
- English
- ISSN :
- 00223263
- Volume :
- 73
- Issue :
- 7
- Database :
- Academic Search Index
- Journal :
- Journal of Organic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 31830610
- Full Text :
- https://doi.org/10.1021/jo702720a